BR112022004989A2 - Simultaneous dehydration, dimerization, and metathesis of c2-c5 alcohols - Google Patents
Simultaneous dehydration, dimerization, and metathesis of c2-c5 alcoholsInfo
- Publication number
- BR112022004989A2 BR112022004989A2 BR112022004989A BR112022004989A BR112022004989A2 BR 112022004989 A2 BR112022004989 A2 BR 112022004989A2 BR 112022004989 A BR112022004989 A BR 112022004989A BR 112022004989 A BR112022004989 A BR 112022004989A BR 112022004989 A2 BR112022004989 A2 BR 112022004989A2
- Authority
- BR
- Brazil
- Prior art keywords
- reactor
- catalyst
- alcohols
- ethylene
- ethanol
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
- C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/28—Molybdenum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/30—Tungsten
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/20—C2-C4 olefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/22—Higher olefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
simultâneas desidratação, dimerização, e metátese de álcoois c2-c5. a presente invenção refere-se a processo de estágio simples para a direta conversão de álcoois, por exemplo, etanol, para misturas olefínicas (c2-c7) com baixos níveis de aromáticos, realizado em um reator simples com dois leitos catalíticos fixos em série, ou dois reatores catalíticos de leito fixo em série, em que o primeiro reator opera a uma temperatura menor ou maior que a temperatura de operação do segundo reator. o processo de transformação de etanol é compreendido por desidratação de etanol a etileno e água em alto rendimento com o primeiro catalisador no primeiro reator, ou via o primeiro leito fixo de catalisador, seguido por alimentação direta de etileno e água para o segundo reator, ou segundo leito fixo de catalisador, com conversão dos referidos etileno e água a uma mistura olefínica c2-c7 com o(s) segundo(s) catalisador(es) em alto rendimento com formação mínima de composto aromático.simultaneous dehydration, dimerization, and metathesis of c2-c5 alcohols. the present invention relates to a single stage process for the direct conversion of alcohols, eg ethanol, to olefinic mixtures (c2-c7) with low levels of aromatics, carried out in a single reactor with two catalytic beds fixed in series, or two fixed bed catalytic reactors in series, where the first reactor operates at a temperature lower or higher than the operating temperature of the second reactor. the ethanol transformation process is comprised of dehydration of ethanol to ethylene and water in high yield with the first catalyst in the first reactor, or via the first fixed bed of catalyst, followed by direct feeding of ethylene and water to the second reactor, or second fixed bed of catalyst, with conversion of said ethylene and water to a c2-c7 olefinic mixture with the second catalyst(s) in high yield with minimal formation of aromatic compound.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201962908457P | 2019-09-30 | 2019-09-30 | |
US201962910948P | 2019-10-04 | 2019-10-04 | |
US201962914837P | 2019-10-14 | 2019-10-14 | |
US201962938172P | 2019-11-20 | 2019-11-20 | |
PCT/US2020/053312 WO2021067294A1 (en) | 2019-09-30 | 2020-09-29 | Simultaneous dehydration, dimerization, and metathesis of c2-c5 alcohols |
Publications (1)
Publication Number | Publication Date |
---|---|
BR112022004989A2 true BR112022004989A2 (en) | 2022-06-21 |
Family
ID=75336504
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112022004989A BR112022004989A2 (en) | 2019-09-30 | 2020-09-29 | Simultaneous dehydration, dimerization, and metathesis of c2-c5 alcohols |
Country Status (7)
Country | Link |
---|---|
US (1) | US20220227685A1 (en) |
EP (1) | EP4038040A4 (en) |
CN (1) | CN114929653A (en) |
BR (1) | BR112022004989A2 (en) |
CA (1) | CA3154623A1 (en) |
MX (1) | MX2022003604A (en) |
WO (1) | WO2021067294A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2022262789A1 (en) * | 2021-04-23 | 2023-10-26 | Gevo, Inc. | Systems and processes for catalytic conversion of c1-c5 alcohols to c2-c5 olefin mixtures |
WO2024091452A1 (en) | 2022-10-27 | 2024-05-02 | Gevo, Inc. | Processes for catalytic conversion of c1-c5 alcohols to c2-c5 olefin mixtures |
WO2024089254A1 (en) | 2022-10-28 | 2024-05-02 | Basf Se | Process for the manufacture of a c4-olefin-derived chemical of interest, in particular citral, from renewably-sourced ethanol |
WO2024089252A1 (en) | 2022-10-28 | 2024-05-02 | Basf Se | Process for the manufacture of a propylene-derived chemical of interest, in particular an acrylic ester, from renewably-sourced ethanol |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4049573A (en) * | 1976-02-05 | 1977-09-20 | Mobil Oil Corporation | Zeolite catalyst containing oxide of boron or magnesium |
US4590320A (en) * | 1984-08-31 | 1986-05-20 | Mobil Oil Corporation | Conversion of methanol to olefins in a tubular reactor with light olefin co-feeding |
US7371916B1 (en) * | 2004-09-16 | 2008-05-13 | Uop Llc | Conversion of an alcoholic oxygenate to propylene using moving bed technology and an etherification step |
JPWO2007055361A1 (en) * | 2005-11-14 | 2009-04-30 | 三井化学株式会社 | Method for producing propylene containing biomass-derived carbon |
CN103274884A (en) * | 2008-02-07 | 2013-09-04 | 道达尔石油化学产品研究弗吕公司 | Process to make olefins from ethanol |
EP2521705A4 (en) * | 2010-01-08 | 2014-06-18 | Gevo Inc | Integrated methods of preparing renewable chemicals |
EP2374780A1 (en) * | 2010-04-09 | 2011-10-12 | Total Petrochemicals Research Feluy | Production of propylene via simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts followed by metathesis |
MY161426A (en) * | 2010-03-15 | 2017-04-14 | Total Res & Technology Feluy | Production of propylene via simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts followed by metathesis |
BR112013002360A2 (en) * | 2010-08-03 | 2016-05-24 | Total Res & Technology Feluy | combined process to make cellefins from an isobutanol |
CN107312569B (en) * | 2016-04-26 | 2019-05-21 | 神华集团有限责任公司 | A kind of isoparaffin solvent oil that F- T synthesis naphtha produces the method for isoparaffin solvent oil and obtained by this method |
CN110325493B (en) * | 2016-10-14 | 2022-12-20 | 吉沃公司 | High yield of C from bioalcohols 2 -C 8 Conversion of olefin mixtures into jet and/or diesel fuels |
-
2020
- 2020-09-29 MX MX2022003604A patent/MX2022003604A/en unknown
- 2020-09-29 EP EP20871829.6A patent/EP4038040A4/en active Pending
- 2020-09-29 BR BR112022004989A patent/BR112022004989A2/en unknown
- 2020-09-29 CA CA3154623A patent/CA3154623A1/en active Pending
- 2020-09-29 WO PCT/US2020/053312 patent/WO2021067294A1/en unknown
- 2020-09-29 CN CN202080068569.5A patent/CN114929653A/en active Pending
-
2022
- 2022-03-16 US US17/695,993 patent/US20220227685A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
MX2022003604A (en) | 2022-05-30 |
CA3154623A1 (en) | 2021-04-08 |
US20220227685A1 (en) | 2022-07-21 |
EP4038040A4 (en) | 2024-01-10 |
EP4038040A1 (en) | 2022-08-10 |
CN114929653A (en) | 2022-08-19 |
WO2021067294A1 (en) | 2021-04-08 |
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